Androsterone glucuronide

Androsterone glucuronide
Names
	IUPAC name 17-Oxo-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
	Systematic IUPAC name (2S,3S,4S,5R,6R)-6-{[(3aS,3bR,5aS,7R,9aS,9bS,11aS)-9a,11a-Dimethyl-1-oxohexadecahydro-1H-cyclopenta[a]pheananthren-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
	Other names ADT-G; 5α-Androstan-3α-ol-17-one 3-glucuronide
Identifiers
CAS Number	1852-43-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28832;
ChemSpider	102793;
KEGG	C11135;
PubChem CID	114833;
UNII	IMD4XD0W3U ;
CompTox Dashboard (EPA)	DTXSID80862764 ;
	InChI InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1 Key: VFUIRAVTUVCQTF-BSOWLZGZSA-N;
	SMILES C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O;
Properties
Chemical formula	C25H38O8
Molar mass	466.571 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Androsterone glucuronide (ADT-G) is a major circulating and urinary metabolite of testosterone and dihydrotestosterone (DHT).^[1] It accounts for 93% of total androgen glucuronides in women.^[1] ADT-G is formed from androsterone by UDP-glucuronosyltransferases, with the major enzymes being UGT2B15 and UGT2B17.^[1] It is a marker of acne in women while androstanediol glucuronide is a marker of hirsutism (excess hair growth) in women.^[2]

Relevance in women's health

Quantification of ADT-G and 3α-diol-G levels in Serum (blood) is an effective means of assessing androgen content in blood and androgenic activity in women.^[3] Androsterone glucuronide content can be estimated using Liquid chromatography–mass spectrometry.^[3]^[4] If an unusual level of ADT-G is observed in the blood (either an elevated or decreased amount), proper treatment plans can be developed in order to treat related symptoms.^[3]

Elevated levels of androsterone glucuronide in the blood have been observed in adult females who present with inflammatory acne.^[5] The introduction of therapeutic antiandrogen treatment and the use of an oral Contraceptive by women who are affected with androsterone related acne can decrease the amount of inflammatory acne present.^[5]

References

^ ^a ^b ^c "Human Metabolome Database: Showing metabocard for Androsterone glucuronide (HMDB0002829)".
^ Jerome F. Strauss, III; Robert L. Barbieri (13 September 2013). Yen and Jaffe's Reproductive Endocrinology. Elsevier Health Sciences. pp. 837–. ISBN 978-1-4557-2758-2.
^ ^a ^b ^c Labrie, Fernand; Bélanger, Alain; Bélanger, Patrick; Bérubé, René; Martel, Céline; Cusan, Leonello; Gomez, José; Candas, Bernard; Castiel, Isabelle; Chaussade, Véronique; Deloche, Claire; Leclaire, Jacques (2006-06-01). "Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women". The Journal of Steroid Biochemistry and Molecular Biology. 99 (4): 182–188. doi:10.1016/j.jsbmb.2006.02.004. ISSN 0960-0760.
^ Ke, Yuyong; Gonthier, Renaud; Isabelle, Maxim; Bertin, Jonathan; Simard, Jean-Nicolas; Dury, Alain Y.; Labrie, Fernand (2015-05-01). "A rapid and sensitive UPLC–MS/MS method for the simultaneous quantification of serum androsterone glucuronide, etiocholanolone glucuronide, and androstan-3α, 17β diol 17-glucuronide in postmenopausal women". The Journal of Steroid Biochemistry and Molecular Biology. 149: 146–152. doi:10.1016/j.jsbmb.2015.02.009. ISSN 0960-0760.
^ ^a ^b Carmina, E.; Godwin, A. J.; Stanczyk, F. Z.; Lippman, J. S.; Lobo, R. A. (2002-10-01). "The association of serum androsterone glucuronide with inflammatory lesions in women with adult acne1". Journal of Endocrinological Investigation. 25 (9): 765–768. doi:10.1007/BF03345509. ISSN 1720-8386.

External links

Metabocard for Androsterone Glucuronide (HMDB02829) – Human Metabolome Database

[HMDB-1] "Human Metabolome Database: Showing metabocard for Androsterone glucuronide (HMDB0002829)".

[IIIBarbieri2013-2] Jerome F. Strauss, III; Robert L. Barbieri (13 September 2013). Yen and Jaffe's Reproductive Endocrinology. Elsevier Health Sciences. pp. 837–. ISBN 978-1-4557-2758-2.

[:0-3] Labrie, Fernand; Bélanger, Alain; Bélanger, Patrick; Bérubé, René; Martel, Céline; Cusan, Leonello; Gomez, José; Candas, Bernard; Castiel, Isabelle; Chaussade, Véronique; Deloche, Claire; Leclaire, Jacques (2006-06-01). "Androgen glucuronides, instead of testosterone, as the new markers of androgenic activity in women". The Journal of Steroid Biochemistry and Molecular Biology. 99 (4): 182–188. doi:10.1016/j.jsbmb.2006.02.004. ISSN 0960-0760.

[4] Ke, Yuyong; Gonthier, Renaud; Isabelle, Maxim; Bertin, Jonathan; Simard, Jean-Nicolas; Dury, Alain Y.; Labrie, Fernand (2015-05-01). "A rapid and sensitive UPLC–MS/MS method for the simultaneous quantification of serum androsterone glucuronide, etiocholanolone glucuronide, and androstan-3α, 17β diol 17-glucuronide in postmenopausal women". The Journal of Steroid Biochemistry and Molecular Biology. 149: 146–152. doi:10.1016/j.jsbmb.2015.02.009. ISSN 0960-0760.

[:1-5] Carmina, E.; Godwin, A. J.; Stanczyk, F. Z.; Lippman, J. S.; Lobo, R. A. (2002-10-01). "The association of serum androsterone glucuronide with inflammatory lesions in women with adult acne1". Journal of Endocrinological Investigation. 25 (9): 765–768. doi:10.1007/BF03345509. ISSN 1720-8386.

[1]

[2]

[3]

[4]

[5]

Relevance in women's health

See also

References

External links